Synthesis of 1,1,3,3-Tetraalkylisoindolines Using a Microwave-Assisted Grignard Reaction

Article

<< Previous

Next >>

Contents Vol 61(3)

doi:10.1071/CH08008

Synthesis of 1,1,3,3-Tetraalkylisoindolines Using a Microwave-Assisted Grignard Reaction

Richard C. Foitzik ^A, Steven E. Bottle ^B, Jonathan M. White ^C ^D, Peter J. Scammells ^A ^E

^A Medicinal Chemistry and Drug Action, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville VIC 3052, Australia.
^B School of Physical Sciences and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane QLD 4001, Australia.
^C School of Chemistry, University of Melbourne, VIC 3010, Australia.
^D Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, VIC 3010, Australia.
^E Corresponding author. Email: peter.scammells@vcp.monash.edu.au





	PDF (236 KB) $25



	Export Citation

Print

Australian Journal of Chemistry 61(3) 168–171 http://dx.doi.org/10.1071/CH08008
Submitted: 11 January 2008 Accepted: 16 February 2008 Published online: 26 March 2008

Abstract

1,1,3,3-Tetraalkylisoindolines are important intermediates in the preparation of stable nitroxides, such as 1,1,3,3-tetramethylisoindolin-2-oxyl, 1, and 1,1,3,3-tetraethylisoindolin-2-oxyl, 2. The limiting step in their preparation is the Grignard reaction between N-benzylphthalimide and the appropriate alkyl magnesium bromide, which typically proceeds in yields of ~28–40%. A microwave-assisted variation of this reaction has been optimized to give improved yields and reduced reaction times (45–60% and 2 h, respectively).